The Outlaw and the Amazon Ch. 07

This is part of a series. You may not understand things if you start here.

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"Will?" Sitala, cuddled up to Will, asked.

"Yes?"

"Why are you out here, anyway? You don't look like you belong here."

"Oh. Well, might as well tell you. Do you want a summary or the whole thing?" Will asked Sitala.

"The whole thing, please." Sitala requested.

"Very well then. It went like this..."

.............

Willcock was going home from training when a fellow trainee (Jacob? He wasn't sure.) approached him.

"Hey, Willcock! I got a sexfight against a hot babe lined up. I just need someone to join the team." The man greeted Willcock enthusiastically.

"Wait, you need a teammate against A hot babe? Singular?" Willcock was skeptical of this.

"Man, a girl like her is worth it. You can hold her down, I'll do the hard work. Come on, you'll see. It'll be fun!" The trainee promised.

"Alright. But first, tell me the rules and bets, if there are any." Willcock requested, skeptical.

"Oh. Uh. Sure, man." The trainee nervously answered. "So. We rented a big hotel suite, five rooms. No clothes, no holds barred. Fighting until exhaustion or submission, teaming up is allowed."

"No bets?" Willcock decided to ask again, just to make sure.

"Uhhh, wellll..." The trainee mumbled.

"Come on. You can't expect me to accept a bet without knowing what it is!" Willcock exclaimed. "That would be insane!"

"Fine! Fine. The bet is absolute obedience for one day. If we win, we'll get to share her. If she wins, she gets us both." The trainee admitted.

"I'm only participating if I'm excluded from that bet. I don't have time to be someone's slave." Willcock made his conditions clear. If everything was normal and the trainee was just bad at expressing it, then there wasn't a reason to refuse. Besides, being present would put him in a position to intervene if there was something criminal or otherwise wrong going on.

The trainee sighed. "I'll see what I can do."

They reached the hotel and opened the door to their room. Two women stood there. One had long, dark hair, and brown eyes. When she noticed Willcock, her eyes started roaming over him, and a blush crept up her cheeks. Through her tight clothes, one could see powerful muscles and large breasts. The other girl had golden eyes, and shorter, blonde hair tied into a braid with a black ribbon. She was fit, without bulging muscles, but not a fragile maiden either, with a modest chest, but she radiated confidence and contempt.

"I knew you would try something underhanded, Jake," She addressed the trainee who invited Willcock. "so I invited a friend of my own. Hope you don't mind me making things fair."

"Hold on! Hold on. Jake, there seems to be a lot you haven't mentioned here." Willcock, mildly glad she called Jake by name and spared Willcock the embarrassment of misnaming him, interjected. "I would like to know the rules and stakes, this time from everyone involved."

"Well, it's going to be two on two, no clothes, winners get losers as slaves for a day." She answered, not sparing him a glance.

"In that case, I'm out. As I have told Jake, I don't have time to be a slave. And by the sound of it, there is some history there, history I would rather not get swept in." Willcock declared and turned to leave.

"W-wait!" The black-haired lady stammered out. When Willcock turned around, she continued. "H-how about a simple sexfight? No rules, and no bets? J-just the two of us?"

Willcock chuckled to himself. "If everyone else agrees..." He glanced at the blonde and Jake.

The blonde sighed. "Really, Anna? He came here with Jake. You can't trust anyone who associates with Jake."

"Hey!" Jake protested. "How dare you insult me, you slut!"

"Fuck off, Jake." The blonde hissed at Jake. "The only reason I accepted was to get a chance to show you how inferior you are. A sissy like you doesn't get to call me a slut."

"Hold on, now. I barely know him. He just approached me on the street and asked if I wanted in on a sexfight." Willcock clarified.

The blonde gave him a hard look. "Well, Anna, if you want to, you can have him. I'll handle this cockroach just fine."

"Alright then. I am Willcock, of house Cockwell. May I have your name, lady?" He turned away from Jame and the blonde and bowed to Anna.

Blushing even more, she replied, "I'm Anna, of house Winbrook."

"Wait a second. Willcock? Do you know Amanda, by any chance?" The blonde interjected.

"You are interrupting," Will noted. "but yes. We acquainted ourselves during the great sexbattle."

The blonde licked her lips. "Then how about this: We make it a two on two. Me against Jake, and you against Anna. No interference with the other pair, but if the winners are from opposing teams, they fight to decide the overall victor. Our little bet applies only to me and Jake, and is dependent on the outcome of our duel, not on which team wins. Deal?"

"And now you flirt with other men in front of me?" Jake growled at the blonde.

"What? YOU invited me here! If you didn't want me here, you could've just not done so?" Willcock protested.

The blonde also had some things to say: "I will be with whoever I please, thank you very much. You wanting me for yourself does not mean I have to limit myself when I don't want you, creep."

Jake was left sputtering by her rebuttal.

"Wasn't that what this was about in the first place? If you win, I will be at your mercy for a day, and you can use that time to try and convince me to submit to you fully? What, are you afraid now that you don't have an unfair advantage?" The blonde taunted Jake.

"Fine, then." He barked out. "Let's do this. You'll regret that attitude when I put you in your place."

"Are you alright with it, Anna?" Willcock asked, noting she stayed silent during the while exchange.

"...Sure." She nodded.

And on that note, the two pairs separated.

Willcock opened the door for Anna, and once in the room, began to strip. Anna also began to strip once she entered, though it took her much longer than Willcock, as she was trying to gawk at him without him noticing (unsuccessfully).

"If you like what you see, wouldn't feeling it be a lot better?" He teased her.

She grumbled under her breath and sped up, taking off the last of her clothing. She ended by tying her hair with a red ribbon.

Willcock admired her naked body. She was beautiful. Well defined muscles, thick thighs, big, round breasts, and her cute blush came together to form a lovely image.

"W-well?" She asked, shyly averting her gaze. "Am I acceptable to you? O-or do you want to call it off?"

Willcock approached her, step by step, until he was right in front of her, and spoke the whole time. "You are beautiful, cute, and sexy. I can't imagine why this would discourage someone unless they were afraid to lose. If you requested sexfighting practice at the knight trainee barracks, there would be a line of applicants. I don't want to call off the fight. I want to kiss you. May I?"

Anna was as red as a beet now, not thinking of fighting at all. "Y-you may."

And so he kissed her. It was a deep kiss, and his hands weren't idle throughout, trailing along her abs and arm muscles.

When he broke the kiss, Willcock informed the dazed Anna: "I know this is supposed to be a sexfight, but if you want to, we can just make love."

Anna's response was to tackle him to the ground and sit on his stomach, hands pushing down his chest. "You won't get me that easily!"

"Oh, really? Then why don't you fuck me? It's a SEXfight, after all." Willcock taunted her. "I'm sure a strong woman like you won't have any trouble riding me to submission."

Anna pouted and scooted back until she hit Willcock's cock. She then grabbed it and angled it to penetrate her.

She gasped, then ground her crotch into Willcock's. As her inner walls pulsed and squeezed him, Willcock realized that this wasn't going to be as easy as he thought.

"Mmhm~ this good enough for you?" Anna teased him.

Determined to give as good as he got, Will used his hands to force Anna up. He only managed a second before she forced herself back down, but that was enough to alter the angle at which he was entering her and search for a weak spot. He only needed three tries before he found a spot that made her scream in pleasure.

"Aahhh! You - you can't -! Haah! You - hhnngh - you fucker!" Anna certainly didn't appreciate his counterattack.

Content to know that while her walls assaulted his dick, his cock was entrenched in one of her sensitive spots, he let go of her hips and groped her breasts instead.

"They're softer than I expected." He commented, then squeezed harder, causing a long moan from Anna. "And more sensitive, too. This will be fun~."

Anna decided that rather than grinding against Willcock's crotch, a more effective strategy would be to ride him instead.

Willcock grunted when she started to bounce on top of him, then started thrusting up into her as she was riding him, letting go of her breasts and grabbing her hips instead.

"Oh? How bold of you. Let's see how long you last." Willcock continued to banter, seeking to make Anna even more embarrassed and make her show him more of her cute reactions, a wildly successful effort as her only response was to pout at him.

Anna quickly realized that she had underestimated Willcock. She thought her strength and stamina would guarantee her victory when riding, as they had during her previous sexfights, but Willcock matched her wild pace, and even exceeded it, occasionally interrupting her tempo by thrusting as she was lifting herself off of him.

She still thought that she had him, though, and when she realized that as things were, she would not win, it was already too late.

"Ah! Wait, no! Stop! NOOooo~!"

Willcock grinned as Anna came, her bouncing coming to a stop and her moans echoing around the room, then toppled her.

By the time Anna recovered enough to resist, she was on her back, with Willcock pinning her hands to the floor and lining up his cock with her pussy. She prepared herself for penetration but received a kiss instead, which caught her off guard and caused her to not be prepared for his thrusts.

Willcock found Anna adorable. The strong, sexy girl trembled and writhed and blushed and squeezed and moaned and pouted, and he found her irresistible. He let go of her wrists and cupped her cheek with one hand while resuming his attack on her chest with the other.

"You're so adorable and lovely. I see why your friend brought you. Only a few could resist your charm."

Anna knew she was going to cum again, but she'd be damned if she didn't make Willcock cum at least once. Besides, if he was going to be this romantic, then he only deserved a little payback. She kissed back, trying to break his momentum, and wrapped her muscular arms and legs around him, pulling him into her embrace and his cock deeper into her pussy.

"Cum for me," she at first whispered into his ear, then moaned, then cried out, "cum for me, cum with me...!"

And Willcock did, the two orgasming together, and Anna going limp.

"Had enough?" Willcock teased her, blowing in her ear.

"Fine~. I yield. You're better than me." Anna admitted, sulking.

Afterwards, Willcock pried himself out of her embrace and went to the other room to see how Jake and his opponent were doing.

When Willcock entered the room, he found Jake cumming into his opponent who was riding him, with an impressive assortment of luststone weapons, toys, leashes, bottles, and ropes strewn around the room.

She glared down at Jake. "You talked so much about how you were going to make me your bitch, you wanted to make this two-on-one, you even set up all these tools to give yourself an edge, and look at you: under me, helpless, and shooting load after load into my pussy. What a wimp."

Jake's only answer were his screams of pleasure as his opponent wrung him dry.

The lady then looked up and noticed Willcock. "And here comes entertainment. I see you beat Anna, and that means you'll be a better fuck than this idiot."

"She was delightful. Beautiful, strong, adorable, what more could a man want? But yes, I made her submit to her pleasure." Willcock commented. "I am surprised you are that eager to fight someone after you just fought a sexfight."

"Crushing this worm can't even be called a fight." The girl said as she got up, picked up Jake, and carried him to another room, then returned to Willcock.

"The name's Adela, by the way. Just so you know what to scream as I squeeze you dry." The girl confidently stated.

"And mine is Willcock, though you already knew that." Willcock began the fight by hugging her, one hand wrapping around her back while the other groped her ass.

"A tame start, huh? Or are you just afra - mhhm! Mmmhhm~." Adela's attempted taunt was interrupted by a kiss from Willcock, which she enthusiastically returned.

During their ravenous kiss, they both reached for their opponent's genitals, Willcock fingering Adela and Adela jerking Willcock off.

The two opponents moaned into their kiss as they were teased by skilled fingers.

Willcock started to think he had severely underestimated Adela as her slender fingers skillfully danced on his cock, gripping and stroking it, running along its length, and teasing his glans.

Adela likewise found that Willcock was not going to give her an easy victory as his rough, strong fingers hit her sensitive spots with precision few others could achieve.

Willcock broke the kiss and moved his mouth to her neck, covering it with light kisses and love bites. Simultaneously, he moved his hand from her ass to her breasts and fondled them.

As he let go of the kiss, Adela taunted him, only to be interrupted by his renewed assault: "Ha! Giving up? Such a - hmm? Kyaa~ wait, no! Stop biting me! Ah~ ahh hah *gasp* - no, stop, I don't want to lose, I don't wanna lose, Idunwannlose, I - I- NOOooo~!"

Adela swiftly yielded to Willcock's affections, climaxing. When she came down from her orgasm, she found Willcock standing two steps away from her.

Confused, she asked: "Why are you not finishing me off? You could have had your way with me if you just kept up the pressure."

"Because I believe the dominant one should yield their position, returning to a neutral one, when they cause an orgasm. It makes matches more interesting and not as one-sided in favor of whoever got into a good position first." Willcock explained. "I could have just kept you as you were and defeat you that way, but I think we will enjoy fighting on more even grounds more than just a one-sided fuck."

Adela was touched by that. Not many cared for what their opponent wanted beyond how they could use it to win. But if he was going to offer her a chance to reverse things, then she was going to take it. Her answer to his offer was to tackle him to the ground and ride him.

Not willing to just give up, Willcock grabbed her thighs and pounded up into her, drawing a gasp from her with each thrust, until she took his hands and intertwined their fingers, preventing Willcock from fighting back. Or so she thought.

While Willcock couldn't use his hands to angle her and slam her against his cock, he could still thrust into her and try to angle his pelvis to hit a spot in her she hadn't expected him to hit. He still made her gasp and groan, it was just on every third thrust instead of every single one.

Adela realized she couldn't prevent him from fighting back, and decided to ride him even harder.

Willcock, weakened from their mutual masturbation, was not able to resist any longer and came in her.

As Adela sat on him, panting and sporting a smug smirk, Willcock couldn't help but admire her, and decided to voice said admiration. "You're beautiful." When Adela blushed, he continued. "Your confident grin is adorable. Your golden eyes are warm like a sunset. You're fit, and your breasts are perfect handfuls, while your thighs are wide, soft, squishy, and yet still strong."

Adela couldn't bear it anymore, and hid her face behind her hands, trying to conceal the growing blush spreading across her face. This however freed up Willcock's hands, which he used to sit himself upright and pry her hands away from her face.

"Don't hide from me, please." Willcock requested as he peppered her with quick pecks on the mouth. "Don't I deserve to see your cuteness?" He stopped kissing her. "Besides, we are still one-to-one."

That tore Adela out of her fantasies. He almost had her. Just with some sweet words, he could have done whatever he wanted to her and she wouldn't have resisted, and here he was, not taking the opportunity.

It felt less like politeness and more like pity. She pounced, and with the words "Don't you dare underestimate me!" the two started wrestling for position.

Adela ended up on top, holding Willcock's neck between her thighs and sitting on his chest, her fingers once again dancing on his cock. She thought herself victorious, assuming Willcock couldn't meaningfully counterattack.

But he was stronger than she anticipated. Rather than be helplessly trapped by her thighs, she felt her legs being spread and realized that he used his hands to pry her leglock open, putting himself in a position to eat her out.

She couldn't stop him, so she just focused on his cock, hoping to make him orgasm before he made her.

She was doomed from the start. After all, it was not her who was mercilessly teased and seduced and kissed just a few moments prior. To make things worse for her, his technique was good, better than that of the others who managed to force her into a position where she could be eaten out, and most importantly new to her, whereas he had already experienced her technique so he knew what to expect.

She soon realized the futility of her struggle, and accepted defeat, squirting all over his face.

"Are we done? Or do you submit?" Willcock playfully replied from under her. She knew she was done. There could be no riding him down after the kindness he showed her. "Yeah, I submit."

Deciding to reward her for her decision, Willcock resumed his assault, licking, kissing, and sucking on her clit until she had another orgasm.

"And that's that. Looks like I win." Willcock grinned up at her.

After they dressed, he asked a question that was bothering him for a while. "If you don't mind me asking, what is the history between you and Jake? You don't have to answer if you don't want to, of course. Just... curious."

She sighed. "He slapped my ass at a bar, and I whooped his ass back. Since then, he insisted that I was his and his alone, stalked me, and tried to convince me in increasingly elaborate ways to fully submit to him, knowing he couldn't beat me in a fair sexfight - unlike you."

"Oh. I almost assumed something more... two-sided. Well, sucks to suck, I guess."

(End of sexfights. The following is just plot. Warning: mentioned of attempted murder, accidental killing in self-defense, guilt for accidental killing)

The two of them made light conversation until Anna entered the room, after which they continued making small talk, waiting for Jake to recover and return to the room.

They didn't have to wait long, but he wasn't in the mood for small talk. Instead, he brandished a dagger, and with a scream of "If I can't have you, no one can!" leapt at Adela.

Acting on instinct, Willcock leapt into action, and punched him in the chest, knocking him to the side and away from Adela. Unfortunately, he also knocked him towards a table, and Jake's head landed on its corner with a sharp 'crack'.

........

"There was nothing we could do. The healers tried to save him, but the injury was too severe. The court ruled five years of exile, mostly on account of him being the only son of a noble household, and a warning to keep a low profile if I ever return, as they are unlikely to have forgotten." Willcock finished the story.